# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1838903'
_audit_update_record             
;
2018-04-23 deposited with the CCDC.
2018-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         (C6H5)(C6H4)CH2(C3NOH)(C6H4)OCH3
_chemical_formula_sum            'C23 H19 N O2'
_chemical_formula_weight         341.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.4496(8)
_cell_length_b                   14.0100(8)
_cell_length_c                   13.9414(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.260(8)
_cell_angle_gamma                90.00
_cell_volume                     1771.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6735
_cell_measurement_theta_min      4.1950
_cell_measurement_theta_max      26.8670

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9815
_exptl_absorpt_correction_T_max  0.9879
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17411
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.37
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3293
_reflns_number_gt                2891
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0303P)²+0.5466P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3293
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1013
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_restrained_S_all      1.172
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.23532(16) 0.96343(11) 0.91042(13) 0.0563(4) Uani 1 1 d . . .
O1 O 0.11373(12) 1.01466(8) 0.85015(10) 0.0540(3) Uani 1 1 d . . .
O2 O -0.29131(12) 0.90480(8) 0.85229(10) 0.0507(3) Uani 1 1 d . . .
C17 C -0.14822(16) 1.02084(10) 0.80066(11) 0.0349(3) Uani 1 1 d . . .
C16 C -0.01270(16) 0.97214(10) 0.85572(11) 0.0344(3) Uani 1 1 d . . .
C7 C 0.26569(16) 0.52915(11) 0.94052(11) 0.0350(3) Uani 1 1 d . . .
C22 C -0.28829(17) 0.98693(11) 0.80070(12) 0.0380(4) Uani 1 1 d . . .
C12 C 0.30325(17) 0.59937(11) 0.88132(12) 0.0383(4) Uani 1 1 d . . .
H12 H 0.3290 0.5816 0.8241 0.046 Uiso 1 1 calc R . .
C10 C 0.26692(16) 0.72403(11) 0.99114(11) 0.0361(4) Uani 1 1 d . . .
C15 C 0.02243(17) 0.89557(11) 0.91565(12) 0.0399(4) Uani 1 1 d . . .
H15 H -0.0422 0.8526 0.9320 0.048 Uiso 1 1 calc R . .
C13 C 0.27766(19) 0.82797(11) 1.02172(13) 0.0443(4) Uani 1 1 d . . .
H13A H 0.2553 0.8334 1.0853 0.053 Uiso 1 1 calc R . .
H13B H 0.3786 0.8489 1.0318 0.053 Uiso 1 1 calc R . .
C9 C 0.22791(18) 0.65468(12) 1.04955(12) 0.0431(4) Uani 1 1 d . . .
H9 H 0.2021 0.6726 1.1066 0.052 Uiso 1 1 calc R . .
C6 C 0.26835(17) 0.42663(11) 0.91421(11) 0.0380(4) Uani 1 1 d . . .
C18 C -0.14053(19) 1.10553(11) 0.74957(12) 0.0424(4) Uani 1 1 d . . .
H18 H -0.0489 1.1289 0.7483 0.051 Uiso 1 1 calc R . .
C8 C 0.22656(18) 0.55883(12) 1.02457(12) 0.0431(4) Uani 1 1 d . . .
H8 H 0.1990 0.5137 1.0648 0.052 Uiso 1 1 calc R . .
C21 C -0.41383(18) 1.03673(12) 0.75053(13) 0.0463(4) Uani 1 1 d . . .
H21 H -0.5063 1.0137 0.7501 0.056 Uiso 1 1 calc R . .
C11 C 0.30304(17) 0.69491(11) 0.90592(12) 0.0394(4) Uani 1 1 d . . .
H11 H 0.3275 0.7404 0.8647 0.047 Uiso 1 1 calc R . .
C14 C 0.17794(17) 0.89388(11) 0.94856(12) 0.0374(4) Uani 1 1 d . . .
C20 C -0.4019(2) 1.12032(13) 0.70124(13) 0.0505(5) Uani 1 1 d . . .
H20 H -0.4867 1.1534 0.6678 0.061 Uiso 1 1 calc R . .
C5 C 0.37313(19) 0.39149(12) 0.87014(13) 0.0480(4) Uani 1 1 d . . .
H5 H 0.4420 0.4329 0.8566 0.058 Uiso 1 1 calc R . .
C19 C -0.2660(2) 1.15525(12) 0.70096(13) 0.0496(4) Uani 1 1 d . . .
H19 H -0.2588 1.2121 0.6682 0.059 Uiso 1 1 calc R . .
C3 C 0.2756(3) 0.23365(13) 0.86568(15) 0.0649(6) Uani 1 1 d . . .
H3 H 0.2784 0.1693 0.8500 0.078 Uiso 1 1 calc R . .
C4 C 0.3762(2) 0.29584(14) 0.84615(15) 0.0594(5) Uani 1 1 d . . .
H4 H 0.4468 0.2736 0.8167 0.071 Uiso 1 1 calc R . .
C1 C 0.1663(2) 0.36257(13) 0.93261(13) 0.0531(5) Uani 1 1 d . . .
H1 H 0.0945 0.3842 0.9614 0.064 Uiso 1 1 calc R . .
C23 C -0.4287(2) 0.87589(16) 0.86696(18) 0.0680(6) Uani 1 1 d . . .
H23A H -0.4677 0.9268 0.8981 0.102 Uiso 1 1 calc R . .
H23B H -0.4138 0.8205 0.9091 0.102 Uiso 1 1 calc R . .
H23C H -0.4970 0.8610 0.8036 0.102 Uiso 1 1 calc R . .
C2 C 0.1708(3) 0.26699(14) 0.90841(15) 0.0665(6) Uani 1 1 d . . .
H2 H 0.1022 0.2249 0.9212 0.080 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C14 1.299(2) . ?
N1 O1 1.4144(18) . ?
O1 C16 1.3565(18) . ?
O2 C22 1.3615(19) . ?
O2 C23 1.429(2) . ?
C17 C18 1.396(2) . ?
C17 C22 1.407(2) . ?
C17 C16 1.464(2) . ?
C16 C15 1.343(2) . ?
C7 C8 1.388(2) . ?
C7 C12 1.392(2) . ?
C7 C6 1.484(2) . ?
C22 C21 1.385(2) . ?
C12 C11 1.382(2) . ?
C12 H12 0.9300 . ?
C10 C9 1.382(2) . ?
C10 C11 1.386(2) . ?
C10 C13 1.513(2) . ?
C15 C14 1.412(2) . ?
C15 H15 0.9300 . ?
C13 C14 1.498(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C9 C8 1.386(2) . ?
C9 H9 0.9300 . ?
C6 C1 1.393(2) . ?
C6 C5 1.393(2) . ?
C18 C19 1.379(2) . ?
C18 H18 0.9300 . ?
C8 H8 0.9300 . ?
C21 C20 1.378(2) . ?
C21 H21 0.9300 . ?
C11 H11 0.9300 . ?
C20 C19 1.375(3) . ?
C20 H20 0.9300 . ?
C5 C4 1.383(2) . ?
C5 H5 0.9300 . ?
C19 H19 0.9300 . ?
C3 C2 1.373(3) . ?
C3 C4 1.372(3) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C1 C2 1.385(3) . ?
C1 H1 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C2 H2 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 N1 O1 105.13(13) . . ?
C16 O1 N1 108.97(12) . . ?
C22 O2 C23 118.01(14) . . ?
C18 C17 C22 118.08(14) . . ?
C18 C17 C16 120.04(14) . . ?
C22 C17 C16 121.82(14) . . ?
C15 C16 O1 108.55(13) . . ?
C15 C16 C17 136.54(14) . . ?
O1 C16 C17 114.85(13) . . ?
C8 C7 C12 117.46(14) . . ?
C8 C7 C6 121.71(14) . . ?
C12 C7 C6 120.83(14) . . ?
O2 C22 C21 123.42(15) . . ?
O2 C22 C17 116.40(13) . . ?
C21 C22 C17 120.18(15) . . ?
C11 C12 C7 121.26(15) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
C9 C10 C11 117.92(14) . . ?
C9 C10 C13 121.23(15) . . ?
C11 C10 C13 120.77(15) . . ?
C16 C15 C14 105.60(14) . . ?
C16 C15 H15 127.2 . . ?
C14 C15 H15 127.2 . . ?
C14 C13 C10 114.95(13) . . ?
C14 C13 H13A 108.5 . . ?
C10 C13 H13A 108.5 . . ?
C14 C13 H13B 108.5 . . ?
C10 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C10 C9 C8 121.19(15) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C1 C6 C5 117.90(16) . . ?
C1 C6 C7 121.16(15) . . ?
C5 C6 C7 120.95(15) . . ?
C19 C18 C17 121.31(16) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C9 C8 C7 121.10(15) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C20 C21 C22 120.11(16) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C12 C11 C10 121.03(15) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
N1 C14 C15 111.73(14) . . ?
N1 C14 C13 119.09(15) . . ?
C15 C14 C13 129.11(15) . . ?
C19 C20 C21 120.70(16) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C4 C5 C6 120.98(18) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C20 C19 C18 119.61(16) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C2 C3 C4 119.62(18) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C2 C1 C6 120.52(19) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C3 C2 C1 120.68(19) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 N1 O1 C16 0.09(19) . . . . ?
N1 O1 C16 C15 -0.76(18) . . . . ?
N1 O1 C16 C17 177.00(13) . . . . ?
C18 C17 C16 C15 175.57(18) . . . . ?
C22 C17 C16 C15 -1.7(3) . . . . ?
C18 C17 C16 O1 -1.3(2) . . . . ?
C22 C17 C16 O1 -178.64(14) . . . . ?
C23 O2 C22 C21 -9.0(2) . . . . ?
C23 O2 C22 C17 170.66(16) . . . . ?
C18 C17 C22 O2 -179.23(13) . . . . ?
C16 C17 C22 O2 -1.9(2) . . . . ?
C18 C17 C22 C21 0.4(2) . . . . ?
C16 C17 C22 C21 177.78(14) . . . . ?
C8 C7 C12 C11 0.7(2) . . . . ?
C6 C7 C12 C11 -179.11(14) . . . . ?
O1 C16 C15 C14 1.07(18) . . . . ?
C17 C16 C15 C14 -175.97(17) . . . . ?
C9 C10 C13 C14 -120.64(17) . . . . ?
C11 C10 C13 C14 62.5(2) . . . . ?
C11 C10 C9 C8 0.8(2) . . . . ?
C13 C10 C9 C8 -176.13(15) . . . . ?
C8 C7 C6 C1 35.0(2) . . . . ?
C12 C7 C6 C1 -145.25(16) . . . . ?
C8 C7 C6 C5 -145.10(16) . . . . ?
C12 C7 C6 C5 34.7(2) . . . . ?
C22 C17 C18 C19 0.4(2) . . . . ?
C16 C17 C18 C19 -176.97(15) . . . . ?
C10 C9 C8 C7 0.6(3) . . . . ?
C12 C7 C8 C9 -1.3(2) . . . . ?
C6 C7 C8 C9 178.46(15) . . . . ?
O2 C22 C21 C20 178.93(15) . . . . ?
C17 C22 C21 C20 -0.7(2) . . . . ?
C7 C12 C11 C10 0.7(2) . . . . ?
C9 C10 C11 C12 -1.4(2) . . . . ?
C13 C10 C11 C12 175.49(14) . . . . ?
O1 N1 C14 C15 0.59(19) . . . . ?
O1 N1 C14 C13 -176.63(14) . . . . ?
C16 C15 C14 N1 -1.06(19) . . . . ?
C16 C15 C14 C13 175.81(15) . . . . ?
C10 C13 C14 N1 -120.68(18) . . . . ?
C10 C13 C14 C15 62.6(2) . . . . ?
C22 C21 C20 C19 0.1(3) . . . . ?
C1 C6 C5 C4 -0.5(2) . . . . ?
C7 C6 C5 C4 179.61(15) . . . . ?
C21 C20 C19 C18 0.7(3) . . . . ?
C17 C18 C19 C20 -1.0(3) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C6 C5 C4 C3 -0.1(3) . . . . ?
C5 C6 C1 C2 0.6(3) . . . . ?
C7 C6 C1 C2 -179.47(16) . . . . ?
C4 C3 C2 C1 -0.4(3) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.066
